Dimethylformamide → 3-Benzyloxy-1-propanol

Participants

Reaction Steps

To a solution of 50.0 g (0.657 mol) of 1,3-propandiol 11 in 500 mL of cosolvent (DMF : THF=3:1) in an ice bath was carefully added 26.3 g (0.657 mol) of 60% sodium hydride and stirred for 1 hour, followed by slow addition of 80.5 g (0.636 mol) of benzyl chloride at 0° C. and stirring at room temperature overnight. After adding 50 mL of water to quench the reaction, the mixture was extracted with ether (2×600 mL). The organic layer was washed with water (50 mL) and Brine (50 mL), dried over anhydrous sodium sulfate and concentrated. Distillation at 118-120° C./5 mmHg gave 54.8 g of a liquid in 50.2% yield. 1H NMR (CDCl3): δ 7.35-7.28 (m, 5H, ArH), 4.51 (s, 2H, ArCH2O), 3.76 (m, 2H, CH2O), 3.65 (t, J=6.0 Hz, 2H, CH2O), 2.58 (m, 1H, OH), 1.85 (p, J=6.0 Hz, 2H, CH2). 13C NMR (CDCl3): δ 137.93, 128.34, 127.60, 127.54, 73.15, 69.15, 61.58, 32.04.

Provenance & Evidence